ES2246922T3 - Compuestos heterociclicos que tienen grupos de sulfonamida. - Google Patents
Compuestos heterociclicos que tienen grupos de sulfonamida.Info
- Publication number
- ES2246922T3 ES2246922T3 ES00985953T ES00985953T ES2246922T3 ES 2246922 T3 ES2246922 T3 ES 2246922T3 ES 00985953 T ES00985953 T ES 00985953T ES 00985953 T ES00985953 T ES 00985953T ES 2246922 T3 ES2246922 T3 ES 2246922T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- atom
- groups
- substituted
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 221
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical group NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims abstract description 49
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 23
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 150000004677 hydrates Chemical class 0.000 claims abstract 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 98
- -1 quinoline compound Chemical class 0.000 claims description 77
- 125000004429 atom Chemical group 0.000 claims description 39
- 206010028980 Neoplasm Diseases 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical group 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 230000001772 anti-angiogenic effect Effects 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 206010027476 Metastases Diseases 0.000 claims description 8
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 230000009401 metastasis Effects 0.000 claims description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 201000003068 rheumatic fever Diseases 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 230000001012 protector Effects 0.000 claims description 3
- 239000011135 tin Substances 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 206010018852 Haematoma Diseases 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 description 234
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 156
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 79
- 239000013078 crystal Substances 0.000 description 70
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 65
- 238000003756 stirring Methods 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 239000002904 solvent Substances 0.000 description 49
- 239000012267 brine Substances 0.000 description 48
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 48
- 239000000203 mixture Substances 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000003921 oil Substances 0.000 description 35
- 235000019198 oils Nutrition 0.000 description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 238000010438 heat treatment Methods 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000000605 extraction Methods 0.000 description 27
- 238000001816 cooling Methods 0.000 description 26
- MBTYRZDRPHSJJS-UHFFFAOYSA-N 8-bromoquinolin-3-amine Chemical compound BrC1=CC=CC2=CC(N)=CN=C21 MBTYRZDRPHSJJS-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 22
- 229960003390 magnesium sulfate Drugs 0.000 description 21
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229940124530 sulfonamide Drugs 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- IRVZMXJKUUYKDG-UHFFFAOYSA-N 1-methoxyisoquinolin-6-amine Chemical compound NC1=CC=C2C(OC)=NC=CC2=C1 IRVZMXJKUUYKDG-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 150000003456 sulfonamides Chemical class 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
- AUEFQGAQNYYPQE-UHFFFAOYSA-N 8-chloroquinolin-3-amine Chemical compound ClC1=CC=CC2=CC(N)=CN=C21 AUEFQGAQNYYPQE-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 230000033115 angiogenesis Effects 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 229940124597 therapeutic agent Drugs 0.000 description 7
- LFNYFPRSHXRDDH-UHFFFAOYSA-N 5-chloroquinolin-2-amine Chemical compound ClC1=CC=CC2=NC(N)=CC=C21 LFNYFPRSHXRDDH-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- TZBKVCUKSMTGMP-UHFFFAOYSA-N 1-chloroisoquinolin-6-amine Chemical compound ClC1=NC=CC2=CC(N)=CC=C21 TZBKVCUKSMTGMP-UHFFFAOYSA-N 0.000 description 5
- KBQIVWNPOZQTTE-UHFFFAOYSA-N 5-bromoquinolin-2-amine Chemical compound BrC1=CC=CC2=NC(N)=CC=C21 KBQIVWNPOZQTTE-UHFFFAOYSA-N 0.000 description 5
- QGMUHKAEGCPBLW-UHFFFAOYSA-N 8-(trifluoromethyl)quinolin-3-amine Chemical compound FC(F)(F)C1=CC=CC2=CC(N)=CN=C21 QGMUHKAEGCPBLW-UHFFFAOYSA-N 0.000 description 5
- YJVFIUNUMMZBAG-UHFFFAOYSA-N 8-iodoquinolin-3-amine Chemical compound IC1=CC=CC2=CC(N)=CN=C21 YJVFIUNUMMZBAG-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 229940073640 magnesium sulfate anhydrous Drugs 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000035755 proliferation Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- KRGIYTRJGBFRDS-UHFFFAOYSA-N 4-chloro-n-(1-chloroisoquinolin-6-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=C(C(Cl)=NC=C2)C2=C1 KRGIYTRJGBFRDS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 208000034656 Contusions Diseases 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000004037 angiogenesis inhibitor Substances 0.000 description 4
- 210000000709 aorta Anatomy 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LAWPGISWUSEBAI-UHFFFAOYSA-N 2-[2-(3-nitrophenyl)ethyl]isoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC(CCN2C(C3=CC=CC=C3C2=O)=O)=C1 LAWPGISWUSEBAI-UHFFFAOYSA-N 0.000 description 3
- YYZYZUVHSCLRKI-UHFFFAOYSA-N 2-chloro-4-methylquinolin-7-amine Chemical compound NC1=CC=C2C(C)=CC(Cl)=NC2=C1 YYZYZUVHSCLRKI-UHFFFAOYSA-N 0.000 description 3
- ZSTSAMJBZLEZOA-UHFFFAOYSA-N 3-aminoquinoline-8-carbonitrile Chemical compound N#CC1=CC=CC2=CC(N)=CN=C21 ZSTSAMJBZLEZOA-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- WEPKDBHGQDETGY-UHFFFAOYSA-N 3-nitrophenylethylamine Chemical compound NCCC1=CC=CC([N+]([O-])=O)=C1 WEPKDBHGQDETGY-UHFFFAOYSA-N 0.000 description 3
- RFCJHUVZURQWCD-UHFFFAOYSA-N 4-bromoisoquinolin-7-amine Chemical compound BrC1=CN=CC2=CC(N)=CC=C21 RFCJHUVZURQWCD-UHFFFAOYSA-N 0.000 description 3
- QEFRPTPYMRJBQM-UHFFFAOYSA-N 4-chloro-N-isoquinolin-6-ylbenzenesulfonamide Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC=1C=C2C=CN=CC2=CC=1 QEFRPTPYMRJBQM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- BDAIESOEOPDQFS-UHFFFAOYSA-N ethyl n-(1-ethylisoquinolin-6-yl)carbamate Chemical compound CCC1=NC=CC2=CC(NC(=O)OCC)=CC=C21 BDAIESOEOPDQFS-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229940091250 magnesium supplement Drugs 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003248 quinolines Chemical group 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003461 sulfonyl halides Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- FNLYFJIEFIZBFC-UHFFFAOYSA-N 1,6-naphthyridin-2-amine Chemical compound C1=NC=CC2=NC(N)=CC=C21 FNLYFJIEFIZBFC-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WBPGKBXFWAKQTO-UHFFFAOYSA-N 1-ethylisoquinolin-6-amine Chemical compound NC1=CC=C2C(CC)=NC=CC2=C1 WBPGKBXFWAKQTO-UHFFFAOYSA-N 0.000 description 2
- VJNMUKGZDONIAN-UHFFFAOYSA-N 1-methylisoquinolin-6-amine Chemical compound NC1=CC=C2C(C)=NC=CC2=C1 VJNMUKGZDONIAN-UHFFFAOYSA-N 0.000 description 2
- WSLXYMBJOUUSBG-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydroisoquinolin-6-yl)ethanamine Chemical compound C1NCCC2=CC(CCN)=CC=C21 WSLXYMBJOUUSBG-UHFFFAOYSA-N 0.000 description 2
- ZPWRCEHGIOOXAS-UHFFFAOYSA-N 2-(3-nitrophenyl)butan-1-amine Chemical compound CCC(CN)C1=CC=CC([N+]([O-])=O)=C1 ZPWRCEHGIOOXAS-UHFFFAOYSA-N 0.000 description 2
- IWHACLUNANOQEU-UHFFFAOYSA-N 2-(3-nitrophenyl)butan-1-ol Chemical compound CCC(CO)C1=CC=CC([N+]([O-])=O)=C1 IWHACLUNANOQEU-UHFFFAOYSA-N 0.000 description 2
- UTHKVMHBSSKKHR-UHFFFAOYSA-N 2-(3-nitrophenyl)propan-1-amine Chemical compound NCC(C)C1=CC=CC([N+]([O-])=O)=C1 UTHKVMHBSSKKHR-UHFFFAOYSA-N 0.000 description 2
- SKDUYYSTQIFXSA-UHFFFAOYSA-N 2-(3-nitrophenyl)propan-1-ol Chemical compound OCC(C)C1=CC=CC([N+]([O-])=O)=C1 SKDUYYSTQIFXSA-UHFFFAOYSA-N 0.000 description 2
- HDCJWVVHZGZYDO-UHFFFAOYSA-N 2-(3-nitrophenyl)propanal Chemical compound O=CC(C)C1=CC=CC([N+]([O-])=O)=C1 HDCJWVVHZGZYDO-UHFFFAOYSA-N 0.000 description 2
- ZKYKRMVSSXLKSB-UHFFFAOYSA-N 2-chloro-1,6-naphthyridine Chemical compound C1=NC=CC2=NC(Cl)=CC=C21 ZKYKRMVSSXLKSB-UHFFFAOYSA-N 0.000 description 2
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical compound C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 description 2
- LWTQIJLYJZDJQP-UHFFFAOYSA-N 3-methylisoquinolin-6-amine Chemical compound NC1=CC=C2C=NC(C)=CC2=C1 LWTQIJLYJZDJQP-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IBCREMOZTIARBM-UHFFFAOYSA-N 4-bromo-7-nitroisoquinoline Chemical compound BrC1=CN=CC2=CC([N+](=O)[O-])=CC=C21 IBCREMOZTIARBM-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- GTVVUFQHJQCSNJ-UHFFFAOYSA-N 4-chloro-n-(1-cyanoisoquinolin-6-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=C(C(=NC=C2)C#N)C2=C1 GTVVUFQHJQCSNJ-UHFFFAOYSA-N 0.000 description 2
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
- WLIUYAMOGFOFSH-UHFFFAOYSA-N 4-cyano-n-(1-methoxyisoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 WLIUYAMOGFOFSH-UHFFFAOYSA-N 0.000 description 2
- VPFJTXJRPJGLHT-UHFFFAOYSA-N 4-ethylisoquinolin-6-amine Chemical compound C1=C(N)C=C2C(CC)=CN=CC2=C1 VPFJTXJRPJGLHT-UHFFFAOYSA-N 0.000 description 2
- JKYYJYWSTZTWKF-UHFFFAOYSA-N 4-methylisoquinolin-6-amine Chemical compound C1=C(N)C=C2C(C)=CN=CC2=C1 JKYYJYWSTZTWKF-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- WBAKCSNFRSJAFE-UHFFFAOYSA-N 7-amino-2-chloroquinoline-4-carboxylic acid Chemical compound C1=CC2=C(C=C1N)N=C(C=C2C(=O)O)Cl WBAKCSNFRSJAFE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HJUKHDWAJQTSFN-UHFFFAOYSA-N 8-chloro-4-ethenylquinolin-3-amine Chemical compound ClC1=CC=CC2=C(C=C)C(N)=CN=C21 HJUKHDWAJQTSFN-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- RRTBXHCBDZCLON-UHFFFAOYSA-N ethyl n-(1-chloroisoquinolin-6-yl)carbamate Chemical compound ClC1=NC=CC2=CC(NC(=O)OCC)=CC=C21 RRTBXHCBDZCLON-UHFFFAOYSA-N 0.000 description 2
- DUWPLIQCPKJTMB-UHFFFAOYSA-N ethyl n-(1-methyl-3,4-dihydroisoquinolin-6-yl)carbamate Chemical compound CC1=NCCC2=CC(NC(=O)OCC)=CC=C21 DUWPLIQCPKJTMB-UHFFFAOYSA-N 0.000 description 2
- KOFFJRHBTGXHJT-UHFFFAOYSA-N ethyl n-(1-methylisoquinolin-6-yl)carbamate Chemical compound CC1=NC=CC2=CC(NC(=O)OCC)=CC=C21 KOFFJRHBTGXHJT-UHFFFAOYSA-N 0.000 description 2
- QMFTYUPBCCAAPO-UHFFFAOYSA-N ethyl n-(3-aminophenyl)carbamate;hydrochloride Chemical compound Cl.CCOC(=O)NC1=CC=CC(N)=C1 QMFTYUPBCCAAPO-UHFFFAOYSA-N 0.000 description 2
- FSBRFQGPBBXMJI-UHFFFAOYSA-N ethyl n-(3-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)carbamate Chemical compound C1NC(C)CC2=CC(NC(=O)OCC)=CC=C21 FSBRFQGPBBXMJI-UHFFFAOYSA-N 0.000 description 2
- APXZFEQMORJNCG-UHFFFAOYSA-N ethyl n-(3-methylisoquinolin-6-yl)carbamate Chemical compound C1=NC(C)=CC2=CC(NC(=O)OCC)=CC=C21 APXZFEQMORJNCG-UHFFFAOYSA-N 0.000 description 2
- IAELXQYKJXYMKB-UHFFFAOYSA-N ethyl n-(4-ethyl-1,2,3,4-tetrahydroisoquinolin-6-yl)carbamate Chemical compound C1NCC(CC)C2=CC(NC(=O)OCC)=CC=C21 IAELXQYKJXYMKB-UHFFFAOYSA-N 0.000 description 2
- FOOFWVJXVGUZPG-UHFFFAOYSA-N ethyl n-(4-ethylisoquinolin-6-yl)carbamate Chemical compound C1=NC=C(CC)C2=CC(NC(=O)OCC)=CC=C21 FOOFWVJXVGUZPG-UHFFFAOYSA-N 0.000 description 2
- RAZCIBFLVNOVAH-UHFFFAOYSA-N ethyl n-(4-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)carbamate Chemical compound C1NCC(C)C2=CC(NC(=O)OCC)=CC=C21 RAZCIBFLVNOVAH-UHFFFAOYSA-N 0.000 description 2
- JFQDEXWRKWNGCS-UHFFFAOYSA-N ethyl n-(4-methylisoquinolin-6-yl)carbamate Chemical compound C1=NC=C(C)C2=CC(NC(=O)OCC)=CC=C21 JFQDEXWRKWNGCS-UHFFFAOYSA-N 0.000 description 2
- QTFQWOZKSYYFIT-UHFFFAOYSA-N ethyl n-[3-(2-aminopropyl)phenyl]carbamate;hydrochloride Chemical compound Cl.CCOC(=O)NC1=CC=CC(CC(C)N)=C1 QTFQWOZKSYYFIT-UHFFFAOYSA-N 0.000 description 2
- HPHQYVSSOMWXMX-UHFFFAOYSA-N ethyl n-isoquinolin-6-ylcarbamate Chemical compound C1=NC=CC2=CC(NC(=O)OCC)=CC=C21 HPHQYVSSOMWXMX-UHFFFAOYSA-N 0.000 description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- NGFCTYXFMDWFRQ-UHFFFAOYSA-N isoquinolin-6-amine Chemical compound C1=NC=CC2=CC(N)=CC=C21 NGFCTYXFMDWFRQ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GRMOQNLSBGIKML-UHFFFAOYSA-N methyl n-(1-methoxyisoquinolin-6-yl)carbamate Chemical compound COC1=NC=CC2=CC(NC(=O)OC)=CC=C21 GRMOQNLSBGIKML-UHFFFAOYSA-N 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- INLVEWAPRIFTRL-UHFFFAOYSA-N n-(1-chloroisoquinolin-6-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C(Cl)=NC=C2)C2=C1 INLVEWAPRIFTRL-UHFFFAOYSA-N 0.000 description 2
- QWEDBNQVADDNBQ-UHFFFAOYSA-N n-[2-(3-nitrophenyl)ethyl]acetamide Chemical compound CC(=O)NCCC1=CC=CC([N+]([O-])=O)=C1 QWEDBNQVADDNBQ-UHFFFAOYSA-N 0.000 description 2
- ROZRPWPUJZDIKT-UHFFFAOYSA-N n-isoquinolin-6-yl-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C=NC=C2)C2=C1 ROZRPWPUJZDIKT-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- GILVLSHRCJXUMI-UHFFFAOYSA-N tert-butyl n-[1-(3-aminophenyl)propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)CC1=CC=CC(N)=C1 GILVLSHRCJXUMI-UHFFFAOYSA-N 0.000 description 2
- BDCUWCXKUWGTIH-UHFFFAOYSA-N tert-butyl n-[1-[3-(ethoxycarbonylamino)phenyl]propan-2-yl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(CC(C)NC(=O)OC(C)(C)C)=C1 BDCUWCXKUWGTIH-UHFFFAOYSA-N 0.000 description 2
- LYUHXMSAHNAMFY-UHFFFAOYSA-N tert-butyl n-[2-(3-aminophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=CC=CC(N)=C1 LYUHXMSAHNAMFY-UHFFFAOYSA-N 0.000 description 2
- OULONWXNHSQMOW-UHFFFAOYSA-N tert-butyl n-[2-(3-aminophenyl)propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC(C)C1=CC=CC(N)=C1 OULONWXNHSQMOW-UHFFFAOYSA-N 0.000 description 2
- MXENBGUKVXVTDI-UHFFFAOYSA-N tert-butyl n-[2-(3-nitrophenyl)butyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC(CC)C1=CC=CC([N+]([O-])=O)=C1 MXENBGUKVXVTDI-UHFFFAOYSA-N 0.000 description 2
- RDJQHAJURXTACJ-UHFFFAOYSA-N tert-butyl n-[2-(3-nitrophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=CC=CC([N+]([O-])=O)=C1 RDJQHAJURXTACJ-UHFFFAOYSA-N 0.000 description 2
- AXCXNBFERVUFAE-UHFFFAOYSA-N tert-butyl n-[2-(3-nitrophenyl)propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC(C)C1=CC=CC([N+]([O-])=O)=C1 AXCXNBFERVUFAE-UHFFFAOYSA-N 0.000 description 2
- FHQKRPXGODNYNT-UHFFFAOYSA-N tert-butyl n-[2-[3-(ethoxycarbonylamino)phenyl]butyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C(CC)CNC(=O)OC(C)(C)C)=C1 FHQKRPXGODNYNT-UHFFFAOYSA-N 0.000 description 2
- KNYMPLKIQXTMCD-UHFFFAOYSA-N tert-butyl n-[2-[3-(ethoxycarbonylamino)phenyl]ethyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(CCNC(=O)OC(C)(C)C)=C1 KNYMPLKIQXTMCD-UHFFFAOYSA-N 0.000 description 2
- ZCLAYJDJDQWTKX-UHFFFAOYSA-N tert-butyl n-[2-[3-(ethoxycarbonylamino)phenyl]propyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C(C)CNC(=O)OC(C)(C)C)=C1 ZCLAYJDJDQWTKX-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical class C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- 150000005058 1,8-naphthyridines Chemical class 0.000 description 1
- RNTCWULFNYNFGI-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)CCC2=C1 RNTCWULFNYNFGI-UHFFFAOYSA-N 0.000 description 1
- ARKIFHPFTHVKDT-UHFFFAOYSA-N 1-(3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=CC([N+]([O-])=O)=C1 ARKIFHPFTHVKDT-UHFFFAOYSA-N 0.000 description 1
- VSPOTMOYDHRALZ-UHFFFAOYSA-N 1-(3-nitrophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC([N+]([O-])=O)=C1 VSPOTMOYDHRALZ-UHFFFAOYSA-N 0.000 description 1
- QNFXLCHANYHGIF-UHFFFAOYSA-N 1-acetyl-2,3-dihydroindole-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C2N(C(=O)C)CCC2=C1 QNFXLCHANYHGIF-UHFFFAOYSA-N 0.000 description 1
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004809 1-methylpropylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- RDTRXYINSVAFBZ-UHFFFAOYSA-N 1-n-ethyl-4-n-(1-methoxyisoquinolin-6-yl)benzene-1,4-disulfonamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1S(=O)(=O)NC1=CC=C(C(OC)=NC=C2)C2=C1 RDTRXYINSVAFBZ-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZQKMVHXJWJNEQG-UHFFFAOYSA-N 1h-1,6-naphthyridin-2-one Chemical compound C1=NC=CC2=NC(O)=CC=C21 ZQKMVHXJWJNEQG-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- RVWYPBARHGPULM-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C2OCCC2=C1 RVWYPBARHGPULM-UHFFFAOYSA-N 0.000 description 1
- BTLFTINUSCKVMH-UHFFFAOYSA-N 2,3-dihydrobenzo[f][1,4]benzoxathiine-7-sulfonyl chloride Chemical compound S1CCOC2=CC=C3C(S(=O)(=O)Cl)=CC=CC3=C21 BTLFTINUSCKVMH-UHFFFAOYSA-N 0.000 description 1
- PWZWTSYUZQZFKE-UHFFFAOYSA-N 2-(3-nitrophenyl)ethanol Chemical compound OCCC1=CC=CC([N+]([O-])=O)=C1 PWZWTSYUZQZFKE-UHFFFAOYSA-N 0.000 description 1
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 1
- AGOVJHIHQJDIHF-UHFFFAOYSA-N 2-benzylsulfanyl-4-methoxy-1h-pyridazine Chemical compound N1C=CC(OC)=CN1SCC1=CC=CC=C1 AGOVJHIHQJDIHF-UHFFFAOYSA-N 0.000 description 1
- LFASASWRXAHYQS-UHFFFAOYSA-N 2-benzylsulfanyl-5-methoxy-1h-pyridazine Chemical compound C1=CC(OC)=CNN1SCC1=CC=CC=C1 LFASASWRXAHYQS-UHFFFAOYSA-N 0.000 description 1
- WRIAMYXQKSDDRP-UHFFFAOYSA-N 2-bromo-6-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1C=O WRIAMYXQKSDDRP-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- CPDPDULCMKOHJT-UHFFFAOYSA-N 2-chloro-4-methoxy-1h-pyridazine Chemical compound COC1=CN(Cl)NC=C1 CPDPDULCMKOHJT-UHFFFAOYSA-N 0.000 description 1
- RZDOUWDCYULHJX-UHFFFAOYSA-N 2-chloro-6-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1C=O RZDOUWDCYULHJX-UHFFFAOYSA-N 0.000 description 1
- KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 1
- UBPDKIDWEADHPP-UHFFFAOYSA-N 2-iodoaniline Chemical compound NC1=CC=CC=C1I UBPDKIDWEADHPP-UHFFFAOYSA-N 0.000 description 1
- 125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 description 1
- SGPZMBMYTNCNFZ-UHFFFAOYSA-N 2-n-(8-chloroquinolin-3-yl)-5-n-ethylpyridine-2,5-disulfonamide Chemical compound N1=CC(S(=O)(=O)NCC)=CC=C1S(=O)(=O)NC1=CN=C(C(Cl)=CC=C2)C2=C1 SGPZMBMYTNCNFZ-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- JNDQYURRUBKBPL-UHFFFAOYSA-N 3-(2-bromo-6-nitrophenyl)prop-2-enenitrile Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1C=CC#N JNDQYURRUBKBPL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- FMFBRTVCIIPXMU-UHFFFAOYSA-N 3-cyano-n-(1-methoxyisoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=CC(C#N)=C1 FMFBRTVCIIPXMU-UHFFFAOYSA-N 0.000 description 1
- 125000004811 3-methylpropylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- OOWOYROCAPTOAX-UHFFFAOYSA-N 3-n-(8-chloroquinolin-3-yl)benzene-1,3-disulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(S(=O)(=O)NC=2C=C3C=CC=C(Cl)C3=NC=2)=C1 OOWOYROCAPTOAX-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- RFYHIJAUGNIPFS-UHFFFAOYSA-N 4,8-dichloroquinoline-3-carboxylic acid Chemical compound ClC1=CC=CC2=C(Cl)C(C(=O)O)=CN=C21 RFYHIJAUGNIPFS-UHFFFAOYSA-N 0.000 description 1
- JKLAQMIGQLDXBK-UHFFFAOYSA-N 4-(methanesulfonamido)-n-(1-methoxyisoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(NS(C)(=O)=O)C=C1 JKLAQMIGQLDXBK-UHFFFAOYSA-N 0.000 description 1
- YBCNNWXUEMWRFT-UHFFFAOYSA-N 4-[(1-methoxyisoquinolin-6-yl)sulfamoyl]benzamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(C(N)=O)C=C1 YBCNNWXUEMWRFT-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- GJSIUJABQJQPCQ-UHFFFAOYSA-N 4-chloro-n-(1,6-naphthyridin-2-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=C(C=NC=C2)C2=N1 GJSIUJABQJQPCQ-UHFFFAOYSA-N 0.000 description 1
- DMVHQBYKRXXHTF-UHFFFAOYSA-N 4-chloro-n-(1-ethoxyisoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C(OCC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 DMVHQBYKRXXHTF-UHFFFAOYSA-N 0.000 description 1
- TWSPMQPIGCAAMK-UHFFFAOYSA-N 4-chloro-n-(1-ethylisoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C(CC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 TWSPMQPIGCAAMK-UHFFFAOYSA-N 0.000 description 1
- HQXJAKWYQIAMIU-UHFFFAOYSA-N 4-chloro-n-(1-methoxyisoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 HQXJAKWYQIAMIU-UHFFFAOYSA-N 0.000 description 1
- JYSNBVRLWFEFAE-UHFFFAOYSA-N 4-chloro-n-(1-methylisoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C(C)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 JYSNBVRLWFEFAE-UHFFFAOYSA-N 0.000 description 1
- JRCDJWOWPGLSEO-UHFFFAOYSA-N 4-chloro-n-(1-oxo-2h-isoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C(O)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 JRCDJWOWPGLSEO-UHFFFAOYSA-N 0.000 description 1
- GJURMCJADKSOEK-UHFFFAOYSA-N 4-chloro-n-(3-methylisoquinolin-6-yl)benzenesulfonamide Chemical compound C=1C=C2C=NC(C)=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 GJURMCJADKSOEK-UHFFFAOYSA-N 0.000 description 1
- LFAPEAAKOYYXJR-UHFFFAOYSA-N 4-chloro-n-(4-ethylisoquinolin-6-yl)benzenesulfonamide Chemical compound C1=C2C(CC)=CN=CC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 LFAPEAAKOYYXJR-UHFFFAOYSA-N 0.000 description 1
- QTPNNRVZJQMUIK-UHFFFAOYSA-N 4-chloro-n-(4-methylisoquinolin-6-yl)benzenesulfonamide Chemical compound C1=C2C(C)=CN=CC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 QTPNNRVZJQMUIK-UHFFFAOYSA-N 0.000 description 1
- PIIXJOPDJRVMSE-UHFFFAOYSA-N 4-chloro-n-(5-chloroquinolin-2-yl)benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC=C(C(Cl)=CC=C2)C2=N1 PIIXJOPDJRVMSE-UHFFFAOYSA-N 0.000 description 1
- NNUZPQOZYZRMFJ-UHFFFAOYSA-N 4-chloro-n-[1-(dimethylamino)isoquinolin-6-yl]benzenesulfonamide Chemical compound C=1C=C2C(N(C)C)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 NNUZPQOZYZRMFJ-UHFFFAOYSA-N 0.000 description 1
- XYBMMKTYHDOICQ-UHFFFAOYSA-N 4-chloro-n-[1-(methylamino)isoquinolin-6-yl]benzenesulfonamide Chemical compound C=1C=C2C(NC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 XYBMMKTYHDOICQ-UHFFFAOYSA-N 0.000 description 1
- KAVUMBQUAKOVEE-UHFFFAOYSA-N 4-chloro-n-[2-oxo-4-(trifluoromethyl)chromen-7-yl]benzenesulfonamide Chemical compound C1=CC=2C(C(F)(F)F)=CC(=O)OC=2C=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 KAVUMBQUAKOVEE-UHFFFAOYSA-N 0.000 description 1
- CVKYFIKOYCXFPE-UHFFFAOYSA-N 4-cyano-n-(8-cyanoquinolin-3-yl)benzenesulfonamide Chemical compound C=1N=C2C(C#N)=CC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 CVKYFIKOYCXFPE-UHFFFAOYSA-N 0.000 description 1
- HORMKGIWUWTHEX-UHFFFAOYSA-N 4-cyano-n-(8-iodoquinolin-3-yl)benzenesulfonamide Chemical compound C=1N=C2C(I)=CC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 HORMKGIWUWTHEX-UHFFFAOYSA-N 0.000 description 1
- NNJMVVVYHYLOSA-UHFFFAOYSA-N 4-cyano-n-(8-methylquinolin-3-yl)benzenesulfonamide Chemical compound C=1N=C2C(C)=CC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 NNJMVVVYHYLOSA-UHFFFAOYSA-N 0.000 description 1
- KFZLKOAINSQSRJ-UHFFFAOYSA-N 4-cyano-n-[8-(trifluoromethyl)quinolin-3-yl]benzenesulfonamide Chemical compound C=1N=C2C(C(F)(F)F)=CC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 KFZLKOAINSQSRJ-UHFFFAOYSA-N 0.000 description 1
- ATDJDOFSSFGJFF-UHFFFAOYSA-N 4-n-(1-chloroisoquinolin-6-yl)-1-n-ethylbenzene-1,4-disulfonamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1S(=O)(=O)NC1=CC=C(C(Cl)=NC=C2)C2=C1 ATDJDOFSSFGJFF-UHFFFAOYSA-N 0.000 description 1
- VPXXVZKUWDDLRE-UHFFFAOYSA-N 4-n-(5-chloroquinolin-2-yl)benzene-1,4-disulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1S(=O)(=O)NC1=CC=C(C(Cl)=CC=C2)C2=N1 VPXXVZKUWDDLRE-UHFFFAOYSA-N 0.000 description 1
- FNEIMPFRVQQOMV-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride Chemical compound C1CCCC2=CC(S(=O)(=O)Cl)=CC=C21 FNEIMPFRVQQOMV-UHFFFAOYSA-N 0.000 description 1
- WQUIYOVBBMPYKL-UHFFFAOYSA-N 6-[(4-chlorophenyl)sulfonylamino]isoquinoline-1-carboxamide Chemical compound C=1C=C2C(C(=O)N)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 WQUIYOVBBMPYKL-UHFFFAOYSA-N 0.000 description 1
- UCNKDJKJRDLKNA-UHFFFAOYSA-N 6-amino-n-(1-methoxyisoquinolin-6-yl)pyridine-3-sulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(N)N=C1 UCNKDJKJRDLKNA-UHFFFAOYSA-N 0.000 description 1
- FMHPLNJKPYYYCC-UHFFFAOYSA-N 6-amino-n-(8-bromoquinolin-3-yl)pyridine-3-sulfonamide Chemical compound C1=NC(N)=CC=C1S(=O)(=O)NC1=CN=C(C(Br)=CC=C2)C2=C1 FMHPLNJKPYYYCC-UHFFFAOYSA-N 0.000 description 1
- SNVVIJBGRVPGBB-UHFFFAOYSA-N 6-chloro-n-(1-methoxyisoquinolin-6-yl)pyridine-3-sulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)N=C1 SNVVIJBGRVPGBB-UHFFFAOYSA-N 0.000 description 1
- JBNOVHJXQSHGRL-UHFFFAOYSA-N 7-amino-4-(trifluoromethyl)coumarin Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N)=CC=C21 JBNOVHJXQSHGRL-UHFFFAOYSA-N 0.000 description 1
- NYHHIPIPUVLUFF-UHFFFAOYSA-N 7-nitroisoquinoline Chemical compound C1=CN=CC2=CC([N+](=O)[O-])=CC=C21 NYHHIPIPUVLUFF-UHFFFAOYSA-N 0.000 description 1
- MXKZSCXYMSXOAO-UHFFFAOYSA-N 7-nitroquinoline Chemical compound C1=CC=NC2=CC([N+](=O)[O-])=CC=C21 MXKZSCXYMSXOAO-UHFFFAOYSA-N 0.000 description 1
- MJQVRYMRWVWXEA-UHFFFAOYSA-N 8-chloro-4-ethenylquinoline-3-carboxylic acid Chemical compound C=CC1=C2C=CC=C(C2=NC=C1C(=O)O)Cl MJQVRYMRWVWXEA-UHFFFAOYSA-N 0.000 description 1
- VQFSUTQDNLFSTH-UHFFFAOYSA-N 8-methylsulfonylquinolin-3-amine Chemical compound NC1=CN=C2C(S(=O)(=O)C)=CC=CC2=C1 VQFSUTQDNLFSTH-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- NXRBQIUYZUZZFE-UHFFFAOYSA-N C1=[N+]([O-])C=CC2=CC(NC(=O)OCC)=CC=C21 Chemical compound C1=[N+]([O-])C=CC2=CC(NC(=O)OCC)=CC=C21 NXRBQIUYZUZZFE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000012422 Collagen Type I Human genes 0.000 description 1
- 108010022452 Collagen Type I Proteins 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- CECMDCJZYHCLQR-UHFFFAOYSA-N N-(4-bromoquinolin-7-yl)-6-chloropyridine-3-sulfonamide Chemical compound BrC1=CC=NC2=CC(=CC=C12)NS(=O)(=O)C=1C=NC(=CC=1)Cl CECMDCJZYHCLQR-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038910 Retinitis Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000001656 angiogenetic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 125000006243 carbonyl protecting group Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical group C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- NSBVMRLTDBAOBT-UHFFFAOYSA-N disulfanylmethylbenzene Chemical compound SSCC1=CC=CC=C1 NSBVMRLTDBAOBT-UHFFFAOYSA-N 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 210000004696 endometrium Anatomy 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- CWDRDUPQVLNILQ-UHFFFAOYSA-N ethyl N-isoquinolin-3-ylcarbamate Chemical compound C(C)OC(=O)NC=1N=CC2=CC=CC=C2C1 CWDRDUPQVLNILQ-UHFFFAOYSA-N 0.000 description 1
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- CHDTZVSQNQAQAC-UHFFFAOYSA-N ethyl n-(1-ethyl-3,4-dihydroisoquinolin-6-yl)carbamate Chemical compound CCC1=NCCC2=CC(NC(=O)OCC)=CC=C21 CHDTZVSQNQAQAC-UHFFFAOYSA-N 0.000 description 1
- KEUMEQNQIGNNLD-UHFFFAOYSA-N ethyl n-(1-ethyl-4-hydroxy-3-oxo-2h-isoquinolin-6-yl)carbamate Chemical compound CCC1=NC(O)=C(O)C2=CC(NC(=O)OCC)=CC=C21 KEUMEQNQIGNNLD-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- JQOAQUXIUNVRQW-UHFFFAOYSA-N hexane Chemical compound CCCCCC.CCCCCC JQOAQUXIUNVRQW-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000002175 menstrual effect Effects 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- OYEVFSJZQTUDDN-UHFFFAOYSA-N methanol;n-methylmethanamine Chemical compound OC.CNC OYEVFSJZQTUDDN-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- RKGIBJNSINGUDT-UHFFFAOYSA-N methoxymethylphosphanium;chloride Chemical compound [Cl-].COC[PH3+] RKGIBJNSINGUDT-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- JDNNHIIDRGFLRP-UHFFFAOYSA-N n-(1-aminoisoquinolin-6-yl)-4-chlorobenzenesulfonamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(Cl)C=C1 JDNNHIIDRGFLRP-UHFFFAOYSA-N 0.000 description 1
- QXCFTBLEXXHEME-UHFFFAOYSA-N n-(1-chloroisoquinolin-6-yl)-4-cyanobenzenesulfonamide Chemical compound C=1C=C2C(Cl)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 QXCFTBLEXXHEME-UHFFFAOYSA-N 0.000 description 1
- YKJJPESFNHWVKH-UHFFFAOYSA-N n-(1-chloroisoquinolin-6-yl)-4-pyrrolidin-1-ylsulfonylbenzenesulfonamide Chemical compound C=1C=C2C(Cl)=NC=CC2=CC=1NS(=O)(=O)C(C=C1)=CC=C1S(=O)(=O)N1CCCC1 YKJJPESFNHWVKH-UHFFFAOYSA-N 0.000 description 1
- ZHZIUMGTQGLGSA-UHFFFAOYSA-N n-(1-methoxyisoquinolin-6-yl)-1-phenylmethanesulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)CC1=CC=CC=C1 ZHZIUMGTQGLGSA-UHFFFAOYSA-N 0.000 description 1
- XZOIQZOIDAMGQJ-UHFFFAOYSA-N n-(1-methoxyisoquinolin-6-yl)-3-methylbenzenesulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=CC(C)=C1 XZOIQZOIDAMGQJ-UHFFFAOYSA-N 0.000 description 1
- VRSJMLJSCJLLHZ-UHFFFAOYSA-N n-(1-methoxyisoquinolin-6-yl)-4-(1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C(C=C1)=CC=C1C1=NC=CS1 VRSJMLJSCJLLHZ-UHFFFAOYSA-N 0.000 description 1
- NLBQAHWTTMTGKN-UHFFFAOYSA-N n-(1-methoxyisoquinolin-6-yl)-4-methylbenzenesulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(C)C=C1 NLBQAHWTTMTGKN-UHFFFAOYSA-N 0.000 description 1
- XZPDZJLSFZRFPH-UHFFFAOYSA-N n-(1-methoxyisoquinolin-6-yl)pyridine-3-sulfonamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=CN=C1 XZPDZJLSFZRFPH-UHFFFAOYSA-N 0.000 description 1
- VTLGVUYXCOGDLV-UHFFFAOYSA-N n-(5-bromoquinolin-2-yl)-4-cyanobenzenesulfonamide Chemical compound C=1C=C2C(Br)=CC=CC2=NC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 VTLGVUYXCOGDLV-UHFFFAOYSA-N 0.000 description 1
- WLOIIPQRJAJXMR-UHFFFAOYSA-N n-(5-bromoquinolin-2-yl)-5-methylpyridine-3-sulfonamide Chemical compound CC1=CN=CC(S(=O)(=O)NC=2N=C3C=CC=C(Br)C3=CC=2)=C1 WLOIIPQRJAJXMR-UHFFFAOYSA-N 0.000 description 1
- LVMLKUCALYIMNC-UHFFFAOYSA-N n-(5-bromoquinolin-2-yl)pyridine-3-sulfonamide Chemical compound C=1C=C2C(Br)=CC=CC2=NC=1NS(=O)(=O)C1=CC=CN=C1 LVMLKUCALYIMNC-UHFFFAOYSA-N 0.000 description 1
- WYICKPXHEFKGNV-UHFFFAOYSA-N n-(5-chloroquinolin-2-yl)-4-cyanobenzenesulfonamide Chemical compound C=1C=C2C(Cl)=CC=CC2=NC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 WYICKPXHEFKGNV-UHFFFAOYSA-N 0.000 description 1
- MGZMVZKFZKMIHR-UHFFFAOYSA-N n-(5-chloroquinolin-2-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C(Cl)=CC=C2)C2=N1 MGZMVZKFZKMIHR-UHFFFAOYSA-N 0.000 description 1
- JNQOVXHEYBDQNQ-UHFFFAOYSA-N n-(5-chloroquinolin-2-yl)-6-ethylpyridine-3-sulfonamide Chemical compound C1=NC(CC)=CC=C1S(=O)(=O)NC1=CC=C(C(Cl)=CC=C2)C2=N1 JNQOVXHEYBDQNQ-UHFFFAOYSA-N 0.000 description 1
- DSPWZFHTCLXVPE-UHFFFAOYSA-N n-(5-ethenylquinolin-2-yl)pyridine-3-sulfonamide Chemical compound C=1C=C2C(C=C)=CC=CC2=NC=1NS(=O)(=O)C1=CC=CN=C1 DSPWZFHTCLXVPE-UHFFFAOYSA-N 0.000 description 1
- DEMLVXAKNUHDOM-UHFFFAOYSA-N n-(6-chloro-8-cyanoquinolin-3-yl)pyridine-3-sulfonamide Chemical compound C=1C2=CC(Cl)=CC(C#N)=C2N=CC=1NS(=O)(=O)C1=CC=CN=C1 DEMLVXAKNUHDOM-UHFFFAOYSA-N 0.000 description 1
- OFJWVIQGNPUHMV-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-2,3-dihydro-1h-indene-5-sulfonamide Chemical compound C1=C2CCCC2=CC(S(=O)(=O)NC=2C=C3C=CC=C(C3=NC=2)Br)=C1 OFJWVIQGNPUHMV-UHFFFAOYSA-N 0.000 description 1
- WDMSPVNLIUFWSB-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-2,3-dihydrobenzo[f][1,4]benzoxathiine-7-sulfonamide Chemical compound S1CCOC2=CC=C3C(S(=O)(=O)NC=4C=C5C=CC=C(C5=NC=4)Br)=CC=CC3=C21 WDMSPVNLIUFWSB-UHFFFAOYSA-N 0.000 description 1
- UJRUELSVOOWWIA-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-3-hydroxybenzenesulfonamide Chemical compound OC1=CC=CC(S(=O)(=O)NC=2C=C3C=CC=C(Br)C3=NC=2)=C1 UJRUELSVOOWWIA-UHFFFAOYSA-N 0.000 description 1
- FGZARYWBZPLDRE-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-3-methoxybenzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NC=2C=C3C=CC=C(Br)C3=NC=2)=C1 FGZARYWBZPLDRE-UHFFFAOYSA-N 0.000 description 1
- SGEYYAFBFYYLJU-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-4-(2-methylsulfonylethyl)benzenesulfonamide Chemical compound C1=CC(CCS(=O)(=O)C)=CC=C1S(=O)(=O)NC1=CN=C(C(Br)=CC=C2)C2=C1 SGEYYAFBFYYLJU-UHFFFAOYSA-N 0.000 description 1
- HRPNDAQCMIGXOE-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-4-(3-methylsulfonylpropyl)benzenesulfonamide Chemical compound C1=CC(CCCS(=O)(=O)C)=CC=C1S(=O)(=O)NC1=CN=C(C(Br)=CC=C2)C2=C1 HRPNDAQCMIGXOE-UHFFFAOYSA-N 0.000 description 1
- KUDZDRIFKOKQPF-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-4-cyanobenzenesulfonamide Chemical compound C=1N=C2C(Br)=CC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 KUDZDRIFKOKQPF-UHFFFAOYSA-N 0.000 description 1
- QRDRIMPJJJLMPS-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-4-fluorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC1=CN=C(C(Br)=CC=C2)C2=C1 QRDRIMPJJJLMPS-UHFFFAOYSA-N 0.000 description 1
- ZKCUKEYQTDRJCL-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-5-cyanopyridine-2-sulfonamide Chemical compound C=1N=C2C(Br)=CC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=N1 ZKCUKEYQTDRJCL-UHFFFAOYSA-N 0.000 description 1
- MDUIFZSMCPKQBC-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-6-chloropyridine-3-sulfonamide Chemical compound C1=NC(Cl)=CC=C1S(=O)(=O)NC1=CN=C(C(Br)=CC=C2)C2=C1 MDUIFZSMCPKQBC-UHFFFAOYSA-N 0.000 description 1
- HGPHQXYKYJSRNB-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-6-ethylpyridine-3-sulfonamide Chemical compound C1=NC(CC)=CC=C1S(=O)(=O)NC1=CN=C(C(Br)=CC=C2)C2=C1 HGPHQXYKYJSRNB-UHFFFAOYSA-N 0.000 description 1
- ISAYQWMNQUHORX-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-6-methylsulfanylpyridine-3-sulfonamide Chemical compound C1=NC(SC)=CC=C1S(=O)(=O)NC1=CN=C(C(Br)=CC=C2)C2=C1 ISAYQWMNQUHORX-UHFFFAOYSA-N 0.000 description 1
- XFHKBLAYJWYCTR-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)-n-(1,2,3,4-tetrahydroisoquinolin-7-ylsulfonyl)acetamide Chemical compound C1CNCC2=CC(S(=O)(=O)N(C=3C=C4C=CC=C(Br)C4=NC=3)C(=O)C)=CC=C21 XFHKBLAYJWYCTR-UHFFFAOYSA-N 0.000 description 1
- QHLKJBGWHSCHGR-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)benzenesulfonamide Chemical compound C=1N=C2C(Br)=CC=CC2=CC=1NS(=O)(=O)C1=CC=CC=C1 QHLKJBGWHSCHGR-UHFFFAOYSA-N 0.000 description 1
- CNVXOZQFGUFQOQ-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)pyridine-3-sulfonamide Chemical compound C=1N=C2C(Br)=CC=CC2=CC=1NS(=O)(=O)C1=CC=CN=C1 CNVXOZQFGUFQOQ-UHFFFAOYSA-N 0.000 description 1
- AVNJOKFETDGMMQ-UHFFFAOYSA-N n-(8-bromoquinolin-3-yl)quinoline-3-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)NC=3C=C4C=CC=C(C4=NC=3)Br)=CN=C21 AVNJOKFETDGMMQ-UHFFFAOYSA-N 0.000 description 1
- ZFRTYYMNFOACAD-UHFFFAOYSA-N n-(8-chloro-4-ethenylquinolin-3-yl)-4-cyanobenzenesulfonamide Chemical compound C=1N=C2C(Cl)=CC=CC2=C(C=C)C=1NS(=O)(=O)C1=CC=C(C#N)C=C1 ZFRTYYMNFOACAD-UHFFFAOYSA-N 0.000 description 1
- XRJCJFWIUYNXKE-UHFFFAOYSA-N n-(8-chloroquinolin-3-yl)-2,3-dihydro-1-benzofuran-5-sulfonamide Chemical compound C1=C2OCCC2=CC(S(=O)(=O)NC=2C=C3C=CC=C(C3=NC=2)Cl)=C1 XRJCJFWIUYNXKE-UHFFFAOYSA-N 0.000 description 1
- PYEXTLNZADWDNV-UHFFFAOYSA-N n-(8-chloroquinolin-3-yl)-3-cyanobenzenesulfonamide Chemical compound C=1N=C2C(Cl)=CC=CC2=CC=1NS(=O)(=O)C1=CC=CC(C#N)=C1 PYEXTLNZADWDNV-UHFFFAOYSA-N 0.000 description 1
- UVNRWLITWAYWSH-UHFFFAOYSA-N n-(8-chloroquinolin-3-yl)-3-methylbenzenesulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)NC=2C=C3C=CC=C(Cl)C3=NC=2)=C1 UVNRWLITWAYWSH-UHFFFAOYSA-N 0.000 description 1
- YVVKNZARJPLESY-UHFFFAOYSA-N n-(8-chloroquinolin-3-yl)-4-cyanobenzenesulfonamide Chemical compound C=1N=C2C(Cl)=CC=CC2=CC=1NS(=O)(=O)C1=CC=C(C#N)C=C1 YVVKNZARJPLESY-UHFFFAOYSA-N 0.000 description 1
- GMVLDIOFUQXUOU-UHFFFAOYSA-N n-(8-chloroquinolin-3-yl)-5,6,7,8-tetrahydronaphthalene-2-sulfonamide Chemical compound C1CCCC2=CC(S(=O)(=O)NC=3C=C4C=CC=C(C4=NC=3)Cl)=CC=C21 GMVLDIOFUQXUOU-UHFFFAOYSA-N 0.000 description 1
- OYYWZRHMYMFXNC-UHFFFAOYSA-N n-(8-chloroquinolin-3-yl)-6-ethylpyridine-3-sulfonamide Chemical compound C1=NC(CC)=CC=C1S(=O)(=O)NC1=CN=C(C(Cl)=CC=C2)C2=C1 OYYWZRHMYMFXNC-UHFFFAOYSA-N 0.000 description 1
- YLXSBMDWBQSHIJ-UHFFFAOYSA-N n-(8-chloroquinolin-3-yl)benzenesulfonamide Chemical compound C=1N=C2C(Cl)=CC=CC2=CC=1NS(=O)(=O)C1=CC=CC=C1 YLXSBMDWBQSHIJ-UHFFFAOYSA-N 0.000 description 1
- GTEWELNSEDPPKM-UHFFFAOYSA-N n-(8-cyanoquinolin-3-yl)pyridine-3-sulfonamide Chemical compound C=1N=C2C(C#N)=CC=CC2=CC=1NS(=O)(=O)C1=CC=CN=C1 GTEWELNSEDPPKM-UHFFFAOYSA-N 0.000 description 1
- NLKFISZYVMETOM-UHFFFAOYSA-N n-(8-hydroxyquinolin-3-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CN=C(C(O)=CC=C2)C2=C1 NLKFISZYVMETOM-UHFFFAOYSA-N 0.000 description 1
- YYBPYXJZBYUBHK-UHFFFAOYSA-N n-(8-methylquinolin-3-yl)pyridine-3-sulfonamide Chemical compound C=1N=C2C(C)=CC=CC2=CC=1NS(=O)(=O)C1=CC=CN=C1 YYBPYXJZBYUBHK-UHFFFAOYSA-N 0.000 description 1
- OQHSRRHYIYISLK-UHFFFAOYSA-N n-[4-[(1-methoxyisoquinolin-6-yl)sulfamoyl]phenyl]acetamide Chemical compound C=1C=C2C(OC)=NC=CC2=CC=1NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 OQHSRRHYIYISLK-UHFFFAOYSA-N 0.000 description 1
- IEXCSHOKMONFQR-UHFFFAOYSA-N n-[8-(trifluoromethyl)quinolin-3-yl]pyridine-3-sulfonamide Chemical compound C=1N=C2C(C(F)(F)F)=CC=CC2=CC=1NS(=O)(=O)C1=CC=CN=C1 IEXCSHOKMONFQR-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- DNDPRBNVOXRWBA-UHFFFAOYSA-N tert-butyl n-[1-(3-aminophenyl)-2-methylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)CC1=CC=CC(N)=C1 DNDPRBNVOXRWBA-UHFFFAOYSA-N 0.000 description 1
- TVCSAVHOOQLSCA-UHFFFAOYSA-N tert-butyl n-[1-(3-nitrophenyl)propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)CC1=CC=CC([N+]([O-])=O)=C1 TVCSAVHOOQLSCA-UHFFFAOYSA-N 0.000 description 1
- JLAICEVQZHBDGJ-UHFFFAOYSA-N tert-butyl n-[2-(3-aminophenyl)butyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC(CC)C1=CC=CC(N)=C1 JLAICEVQZHBDGJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229930195735 unsaturated hydrocarbon Chemical group 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP37548999 | 1999-12-28 | ||
JP37548999 | 1999-12-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2246922T3 true ES2246922T3 (es) | 2006-03-01 |
Family
ID=18505601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES00985953T Expired - Lifetime ES2246922T3 (es) | 1999-12-28 | 2000-12-27 | Compuestos heterociclicos que tienen grupos de sulfonamida. |
Country Status (16)
Country | Link |
---|---|
US (1) | US6787534B2 (fr) |
EP (1) | EP1243583B1 (fr) |
JP (1) | JP4234344B2 (fr) |
KR (1) | KR100641802B1 (fr) |
CN (1) | CN1217936C (fr) |
AT (1) | ATE305302T1 (fr) |
AU (1) | AU776933B2 (fr) |
CA (1) | CA2395772C (fr) |
DE (1) | DE60022906T2 (fr) |
ES (1) | ES2246922T3 (fr) |
HU (1) | HUP0203973A3 (fr) |
MX (1) | MXPA02006474A (fr) |
NO (1) | NO324268B1 (fr) |
NZ (1) | NZ519380A (fr) |
RU (1) | RU2239631C2 (fr) |
WO (1) | WO2001047891A1 (fr) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1481678A4 (fr) * | 2002-03-05 | 2009-12-30 | Eisai R&D Man Co Ltd | Agent antitumoral comprenant une combinaison d'un compose heterocyclique contenant un sulfamide et d'un inhibiteur d'angiogenese |
MXPA04009141A (es) * | 2002-03-21 | 2004-11-26 | Abbott Lab | Promotores de apoptosis, de n-sulfonilurea. |
US7030115B2 (en) | 2002-03-21 | 2006-04-18 | Abbott Laboratories | N-sulfonylurea apoptosis promoters |
EP1731507A1 (fr) | 2005-04-26 | 2006-12-13 | Institut National des Sciences Appliquees de Rouen (INSA) | Nouvelles composées heterocycliques, leur préparation et leur utilisation comme médicaments en particulier comme agents anti-alzheimer |
PL1893612T3 (pl) | 2005-06-22 | 2012-01-31 | Plexxikon Inc | Pochodne pirolo-[2,3-b]pirydyny jako inhibitory kinazy białkowej |
ES2580108T3 (es) * | 2005-07-11 | 2016-08-19 | Aerie Pharmaceuticals, Inc | Compuestos de isoquinolina |
WO2007008942A2 (fr) * | 2005-07-11 | 2007-01-18 | Aerie Pharmaceuticals, Inc. | Derives de [1-(pyridin-4-yl)-methylidene]-hydrazide d'acide phenylamino-acetique et composes associes en tant que modulateurs des kinases du recepteur couple a la proteine g pour le traitement de troubles oculaires |
WO2007044729A2 (fr) * | 2005-10-07 | 2007-04-19 | Exelixis, Inc. | Inhibiteurs de la phosphatidylinositol 3-kinase et procédés pour leur utilisation |
BRPI0707764A2 (pt) * | 2006-02-13 | 2011-05-10 | Hofemann La Roche Ag F | compostos, processo para a sua manufatura, composiÇÕes farmacÊuticas que contÊm, mÉtodo para o tratamento terapÊutico e / ou profilÁtico de enfermidades que sço moduladas por inibidores de l-cpt1 e usos dos compostos |
DE602007011773D1 (de) * | 2006-08-04 | 2011-02-17 | Merz Pharma Gmbh & Co Kgaa | Substituierte pyrazolopyrimidine, ein verfahren zu ihrer herstellung und ihre verwendung als medizin |
EP2068878B1 (fr) | 2006-09-20 | 2019-04-10 | Aerie Pharmaceuticals, Inc. | Inhibiteurs de la rho-kinase |
US8455513B2 (en) | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
TWI425945B (zh) * | 2007-05-28 | 2014-02-11 | Seldar Pharma Inc | 四氫異喹啉-1-酮衍生物或其鹽 |
US8455514B2 (en) | 2008-01-17 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-and 7-amino isoquinoline compounds and methods for making and using the same |
US8450344B2 (en) | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
ES2834451T3 (es) | 2009-05-01 | 2021-06-17 | Aerie Pharmaceuticals Inc | Inhibidores de mecanismo doble para el tratamiento de enfermedades |
US8546399B2 (en) | 2009-05-26 | 2013-10-01 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
US9034875B2 (en) | 2009-05-26 | 2015-05-19 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
US20220315555A1 (en) | 2009-05-26 | 2022-10-06 | Abbvie Inc. | Apoptosis inducing agents for the treatment of cancer and immune and autoimmune diseases |
SG10201704742YA (en) * | 2009-05-26 | 2017-07-28 | Abbvie Ireland Unlimited Co | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
US20120196854A1 (en) | 2009-10-06 | 2012-08-02 | Kyowa Hakko Kirin Co., Ltd. | Pharmaceutical composition comprising aromatic heterocyclic compound |
CA2811805A1 (fr) | 2010-10-29 | 2012-05-03 | Abbvie Inc. | Dispersions solides contenant un agent induisant l'apoptose |
UA113500C2 (xx) | 2010-10-29 | 2017-02-10 | Одержані екструзією розплаву тверді дисперсії, що містять індукуючий апоптоз засіб | |
CN107266435A (zh) | 2010-11-23 | 2017-10-20 | Abbvie 公司 | 细胞凋亡诱导剂的盐和晶形 |
CN103402521B (zh) | 2010-11-23 | 2016-01-20 | 艾伯维巴哈马有限公司 | 使用选择性的bcl-2抑制剂的治疗方法 |
JP5965923B2 (ja) * | 2011-02-24 | 2016-08-10 | ジエンス ハンセン ファーマセウティカル カンパニー リミテッド | プロテインキナーゼ阻害剤としてのリン含有化合物 |
US20140275082A1 (en) | 2013-03-14 | 2014-09-18 | Abbvie Inc. | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases |
CN110396085A (zh) | 2013-03-15 | 2019-11-01 | 爱瑞制药公司 | 联合治疗 |
CN104447536B (zh) * | 2014-10-25 | 2017-04-12 | 大连理工大学 | 一种n‑2‑喹啉基芳基磺酰胺类化合物的制备方法 |
WO2016087593A1 (fr) * | 2014-12-05 | 2016-06-09 | Syngenta Participations Ag | Nouvelles quinolinylamidines fongicides |
US9643927B1 (en) | 2015-11-17 | 2017-05-09 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
AU2015414743B2 (en) | 2015-11-17 | 2019-07-18 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
MX2019002396A (es) | 2016-08-31 | 2019-07-08 | Aerie Pharmaceuticals Inc | Composiciones oftalmicas. |
KR20190135027A (ko) | 2017-03-31 | 2019-12-05 | 에어리 파마슈티컬즈, 인코포레이티드 | 아릴 시클로프로필-아미노-이소퀴놀리닐 아미드 화합물 |
CN111448192B (zh) | 2017-12-15 | 2024-04-12 | 拜耳动物保健有限责任公司 | 用于制备驱蠕虫的4-氨基-喹啉-3-甲酰胺衍生物的方法 |
EP3849555A4 (fr) | 2018-09-14 | 2022-05-04 | Aerie Pharmaceuticals, Inc. | Composés d'amide aryl cyclopropyl-amino-isoquinolinyl |
US20220119350A1 (en) * | 2019-02-22 | 2022-04-21 | Glaukos Corporation | Compounds for the treatment of ocular disease |
WO2021257857A1 (fr) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Composés naphtyridinone en tant qu'inhibiteurs de jak2 v617f |
WO2021257863A1 (fr) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Composés de pyrrolotriazine utilisés en tant qu'inhibiteurs de v617f de jak2 |
EP4175719A1 (fr) | 2020-07-02 | 2023-05-10 | Incyte Corporation | Composés d'urée tricycliques en tant qu'inhibiteurs de v617f de jak2 |
US11767323B2 (en) | 2020-07-02 | 2023-09-26 | Incyte Corporation | Tricyclic pyridone compounds as JAK2 V617F inhibitors |
WO2022046989A1 (fr) | 2020-08-27 | 2022-03-03 | Incyte Corporation | Composés d'urée tricycliques en tant qu'inhibiteurs de v617f de jak2 |
US11919908B2 (en) | 2020-12-21 | 2024-03-05 | Incyte Corporation | Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors |
AR125273A1 (es) | 2021-02-25 | 2023-07-05 | Incyte Corp | Lactamas espirocíclicas como inhibidores de jak2 v617f |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD9688A (fr) * | ||||
DE9688C (de) | T. REMUS in Plauen bei Dresden | Filter | ||
GB662798A (en) | 1948-05-06 | 1951-12-12 | American Cyanamid Co | Improvements in or relating to the production of sulphonamides and intermediates thereof |
DE907739C (de) * | 1949-07-23 | 1954-02-18 | Kalle & Co Ag | Verfahren zur Herstellung von Kopien, besonders Druckformen, mit Hilfe von Diazoverbindungen und dafuer verwendbares lichtempfindliches Material |
US3157684A (en) | 1961-02-13 | 1964-11-17 | Atomic Energy Authority Uk | Tritiated-2-methyl-naphthaquinol-(1, 4)-diphosphoric acids |
US3801321A (en) * | 1972-07-18 | 1974-04-02 | Eastman Kodak Co | Photothermographic element,composition and process |
GB1492029A (en) | 1974-01-30 | 1977-11-16 | Bellon R Lab | 4-oxo-1,4-dihydro-1,6-benzo-(h)-naphthyridine-3-carboxylic acid derivatives useful as anti-bacterial agents and their preparation |
US4343804A (en) * | 1979-03-26 | 1982-08-10 | A. H. Robins Company, Inc. | 4-Amino-3-quinolinecarboxylic acids and esters-antisecretory anti-ulcer compounds |
US4333760A (en) | 1980-08-22 | 1982-06-08 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
JPS59220733A (ja) | 1983-05-30 | 1984-12-12 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
DE3422824A1 (de) | 1984-06-20 | 1986-01-02 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Neue herbizid wirksame sulfonylharnstoffe |
EP0215200B1 (fr) | 1985-06-24 | 1992-09-09 | Merck & Co. Inc. | Utilisation des sulfanilamido quinoxalines pour le traitement des maladies néoplastiques |
WO1988003137A1 (fr) | 1986-10-28 | 1988-05-05 | Smith Kline & French Laboratories Limited | Derives tetrahydroisoquinoline-2-yle d'acides carboxyliques servant d'agents antagonistes de la thromboxane a2 |
US5089633A (en) | 1987-04-28 | 1992-02-18 | Georgia Tech Research Corporation | Substituted isocoumarins |
DE3804990A1 (de) | 1988-02-18 | 1989-08-31 | Basf Ag | Herbizid wirksame, heterocyclisch substituierte sulfonamide |
JPH02149562A (ja) | 1988-11-30 | 1990-06-08 | Nisshin Flour Milling Co Ltd | 相間移動触媒を用いた1,4−ジヒドロピリジン誘導体の製造方法 |
NZ233641A (en) * | 1989-05-16 | 1992-07-28 | Merrell Dow Pharma | Quinoline and thienopyridine derivatives and excitatory amino acid antagonistic pharmaceutical compositions |
JPH03150560A (ja) | 1989-11-08 | 1991-06-26 | Konica Corp | ハロゲン化銀カラー写真感光材料 |
DE4102234A1 (de) | 1991-01-23 | 1992-07-30 | Dresden Arzneimittel | Neue (alpha)-aminochinolinoyl-(3)-penicilline, verfahren zu deren herstellung und diese enthaltende antibakterielle mittel |
JPH06199047A (ja) * | 1993-01-08 | 1994-07-19 | New Oji Paper Co Ltd | 感熱記録体 |
JPH07138493A (ja) | 1993-11-19 | 1995-05-30 | Konica Corp | 金属錯体化合物及び該化合物を用いた光記録媒体 |
US5529999A (en) | 1994-03-04 | 1996-06-25 | Eli Lilly And Company | Antitumor compositions and methods of treatment |
FR2725719B1 (fr) | 1994-10-14 | 1996-12-06 | Jouveinal Inst Rech | Diazepino-indoles inhibiteurs de phosphodiesterases iv |
CA2235481A1 (fr) | 1995-10-23 | 1997-05-01 | Sean M. Kerwin | Compositions et procedes pour le traitement des deficits osseux |
DE19727117A1 (de) | 1997-06-26 | 1999-01-07 | Boehringer Ingelheim Pharma | Phenylalkylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
TW527355B (en) * | 1997-07-02 | 2003-04-11 | Bristol Myers Squibb Co | Inhibitors of farnesyl protein transferase |
JP4039856B2 (ja) * | 2000-02-03 | 2008-01-30 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | インテグリン発現阻害剤 |
-
2000
- 2000-12-27 US US10/149,253 patent/US6787534B2/en not_active Expired - Fee Related
- 2000-12-27 KR KR1020027008281A patent/KR100641802B1/ko not_active IP Right Cessation
- 2000-12-27 HU HU0203973A patent/HUP0203973A3/hu unknown
- 2000-12-27 JP JP2001549363A patent/JP4234344B2/ja not_active Expired - Fee Related
- 2000-12-27 NZ NZ519380A patent/NZ519380A/en not_active IP Right Cessation
- 2000-12-27 AT AT00985953T patent/ATE305302T1/de not_active IP Right Cessation
- 2000-12-27 EP EP00985953A patent/EP1243583B1/fr not_active Expired - Lifetime
- 2000-12-27 RU RU2002120515/04A patent/RU2239631C2/ru not_active IP Right Cessation
- 2000-12-27 DE DE60022906T patent/DE60022906T2/de not_active Expired - Lifetime
- 2000-12-27 ES ES00985953T patent/ES2246922T3/es not_active Expired - Lifetime
- 2000-12-27 CA CA2395772A patent/CA2395772C/fr not_active Expired - Fee Related
- 2000-12-27 CN CN008180059A patent/CN1217936C/zh not_active Expired - Fee Related
- 2000-12-27 MX MXPA02006474A patent/MXPA02006474A/es active IP Right Grant
- 2000-12-27 WO PCT/JP2000/009326 patent/WO2001047891A1/fr active IP Right Grant
- 2000-12-27 AU AU22283/01A patent/AU776933B2/en not_active Ceased
-
2002
- 2002-06-26 NO NO20023097A patent/NO324268B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NZ519380A (en) | 2004-10-29 |
EP1243583B1 (fr) | 2005-09-28 |
EP1243583A4 (fr) | 2003-08-20 |
US20030144507A1 (en) | 2003-07-31 |
CA2395772A1 (fr) | 2001-07-05 |
HUP0203973A3 (en) | 2004-07-28 |
DE60022906D1 (de) | 2006-02-09 |
CN1414952A (zh) | 2003-04-30 |
KR100641802B1 (ko) | 2006-11-02 |
NO324268B1 (no) | 2007-09-17 |
WO2001047891A1 (fr) | 2001-07-05 |
JP4234344B2 (ja) | 2009-03-04 |
AU2228301A (en) | 2001-07-09 |
US6787534B2 (en) | 2004-09-07 |
HUP0203973A2 (hu) | 2003-03-28 |
CA2395772C (fr) | 2010-09-28 |
MXPA02006474A (es) | 2002-11-29 |
CN1217936C (zh) | 2005-09-07 |
DE60022906T2 (de) | 2006-07-06 |
AU776933B2 (en) | 2004-09-23 |
KR20020068388A (ko) | 2002-08-27 |
NO20023097L (no) | 2002-08-28 |
EP1243583A1 (fr) | 2002-09-25 |
RU2002120515A (ru) | 2004-01-10 |
ATE305302T1 (de) | 2005-10-15 |
NO20023097D0 (no) | 2002-06-26 |
RU2239631C2 (ru) | 2004-11-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES2246922T3 (es) | Compuestos heterociclicos que tienen grupos de sulfonamida. | |
CA2399001C (fr) | Inhibiteur de l'expression de l'integrine | |
TWI287004B (en) | A pyridone derivative having an affinity effect for cannabinoid 2 type receptor | |
TWI295670B (en) | Vanilloid receptor ligands and their use in treatments | |
US20150218120A1 (en) | Hiv integrase inhibitors | |
EP2509954A1 (fr) | 4-oxo-1h-quinoline-3-carboxamides utiles comme modulateurs des transporteurs de cassette se liant à l'atp | |
AU2012382875A1 (en) | Compound as WNT signaling inhibitor, composition, and use thereof | |
CA2871599A1 (fr) | Derives d'imidazothiadiazole et d'imidazopyridazine utiles comme inhibiteurs des recepteurs 4 actives par les proteases (par4) pour traiter l'agregation plaquettaire | |
JP2006521382A (ja) | Akt(プロテインキナーゼb)阻害剤 | |
CN107098846A (zh) | N-酰基磺酰胺类FBPase抑制剂、其制备方法、药物组合物及用途 | |
JP2000517301A (ja) | テトラヒドロイソキノリン誘導体およびそれらの薬理学的使用 | |
AU2003255149A1 (en) | 4-(substituted aryl)-5-hydroxyisoquinolinone derivative | |
ES2236288T3 (es) | 6-heteroarilfenantridinas. | |
JP7144863B2 (ja) | イソキノリン化合物、その調製の方法、およびベータガラクトシダーゼの活性の変質に伴う状態におけるその治療的使用 |